3 Bedroom Villas & Apartments

Grand Cayman offers a number of three-bedroom apartments ideal for a family or small group of friends. Check back often as we’re always adding more options for great places to stay.

Booking with us costs the same as booking directly and you get the benefit of our personal knowledge, recommendations, and assistance. Have a look at the options below or better yet, call (UK) 0207 112 0019 or email cayman@fleewinter.com for advice and to book your Cayman Islands holiday.

We guarantee our prices are the same as booking direct

Everything you book with us is bonded so you have full financial protection

Closely monitored villas and apartments ensures you get the best service

Most importantly, you will get personal unbiased advice from a genuine expert and we’d love to help plan your trip

Fully bonded ATOL protected packaged holidays, with direct flights four times a week offered by British Airways

Grand Cayman

Glorious beaches, luxurious hotels, beautiful villas, incredible dining opportunities, blue iguanas, a bit of history and culture, a sandbar inhabited by stingrays, and an endless variety of ways to keep busy, Grand Cayman offers a beach holiday with something more than sand and sea.

Cayman Brac

Named for its breathtaking bluff, the Brac is an ideal destination for those seeking a beautiful setting with the option to get away from it all or keep busy.

Little Cayman

With a Robinson Crusoe feel, Little Cayman is the place to be if you want to get away from it all. Incredible diving, one small village, and not much else!

Website Search

Search for:

Property Code Search

Property Code:

Cayman Islands News and Reviews

Fleewinter is Guardian Award Winner!

We are very proud of the holidays and service we provide our customers, and were over-the-moon to win the best Short Break Tour Operator 2014 award from the Guardian & Observer Newspaper. We also only missed best overall small tour operator by 0.8%! Many thanks for everyone who voted for us.

Itineraries on Iphones!

Today we officially launch our new system whereby all our customers have the option to have their travel documents delivered to their phone or tablet using the Vamoos app. It includes interactive maps, real time weather forecast plus of course our famous destination guides. Currently available on iphone and ipad and soon to follow on other devices. If you are travelling this summer don’t forget to ask us

JUST 2 DAYS LEFT TO VOTE!!!

We’re looking for people to take two mins to vote for Fleewinter in this years Guardian Travel Awards! Just click on the following link – http://www.global-research.net/guta/start.asp and under tour operator type in ‘fleewinter’ and rate our performance! You can pretty much ignore all other boxes and click submit at the end! Thank you so much!

Guardian Travel Awards 2014

This year we are in the running for the Guardian’s ‘Best Small Tour Operator’ Award and we would REALLY, REALLY, REALLY like to win! So provided you think we deserve it, we would be so grateful if you would take 2 minutes to fill out the following questionnaire – http://www.global-research.net/guta/start.asp There are just three important boxes and the closing date is Friday 6th June: 1. Scroll down to the Tour Operator section and type Fleewinter into the ‘specify other’ box 2. Rate our performance 3. Then click through to the last page (ignoring the other questions if you wish). Thank you all so very much!!

New website about to launch

Welcome to our new website. We are still transferring some of the sections but please let us know what you think of it as it has been the biggest change we have made since Fleewinter was establish more than 10 years ago

Unlike most tour operators and booking agents everything you book with Fleewinter is fully protected with a UK government authorised bonding scheme. Most importantly we are also members of AITO – the Association of Independent Tour Operators – a group of small travel companies dedicated to providing quality products and service at great prices.